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WO1999064142A1 - Emulsifiants - Google Patents

Emulsifiants Download PDF

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Publication number
WO1999064142A1
WO1999064142A1 PCT/EP1999/003740 EP9903740W WO9964142A1 WO 1999064142 A1 WO1999064142 A1 WO 1999064142A1 EP 9903740 W EP9903740 W EP 9903740W WO 9964142 A1 WO9964142 A1 WO 9964142A1
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WIPO (PCT)
Prior art keywords
weight
acid
alkyl
emulsifiers
carbon atoms
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PCT/EP1999/003740
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German (de)
English (en)
Inventor
Achim Ansmann
Stefan BRÜNING
Rolf Kawa
Gabriele Strauss
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Cognis Deutschland Gmbh
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Application filed by Cognis Deutschland Gmbh filed Critical Cognis Deutschland Gmbh
Priority to JP2000553200A priority Critical patent/JP2002517306A/ja
Priority to DE59907734T priority patent/DE59907734D1/de
Priority to EP99939776A priority patent/EP1093397B1/fr
Publication of WO1999064142A1 publication Critical patent/WO1999064142A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/34—Higher-molecular-weight carboxylic acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents

Definitions

  • the invention is in the field of cosmetic emulsions and relates to emulsifiers which give emulsions an increased viscosity and improved stability.
  • Polygiycehnpoly-12-hydroxystearate are known emulsifiers for the production of W / O or O / W emulsions.
  • the substances are described, for example, in German Offenlegungsschriften DE-A1 4420516 and DE-A1 19533539 (Henkel).
  • emulsifiers are usually used together with metal soaps of the magnesium, aluminum or zinc stearate type.
  • the invention relates to emulsifiers containing
  • mixtures of polyol poly-12-hydroxystearates with metal soaps of hydroxycarboxylic acids in particular mixtures of polyglycerol poly-12-hydroxy Stearates with zinc ricinoleate not only give emulsions a higher viscosity, but also stabilize them permanently over the entire temperature range from -5 to 45 ° C.
  • the polyol-12-hydroxystearates are known substances which are sold, for example, under the Dehymuls® PGPH brand.
  • the polyol component of the emulsifiers can be derived from substances which have at least two, preferably 3 to 12 and in particular 3 to 8 hydroxyl groups and 2 to 12 carbon atoms. Typical examples are:
  • Alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;
  • Methyl compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
  • Lower alkyl glucosides in particular those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;
  • Sugar alcohols with 5 to 12 carbon atoms such as sorbitol or mannitol,
  • Aminosugars such as glucamine.
  • reaction products based on polyglycerol are of particular importance among the emulsifiers to be used according to the invention because of their excellent performance properties. It has proven particularly advantageous to use selected polyglycins which have the following homolog distribution (the preferred ranges are given in brackets):
  • the metal soaps are preferably the magnesium, aluminum and / or zinc salts of ricinoleic or 12-hydroxystearic acid.
  • the salts can be used alone or in any mixtures.
  • the weight ratio of the two components (a) and (b), based on the solids content, can be in the range from 20:80 to 80:20, preferably 40:60 to 60:40.
  • Polyol poly-12-hydroxystearates are primarily W / O emulsifiers.
  • nonionic surfactants of the alkyl oligoglucoside type by mixing with nonionic surfactants of the alkyl oligoglucoside type, the emulsification behavior can be influenced in a lasting manner, so that O / W emulsifiers result.
  • Mixtures of polyglycerol poly-12-hydroxystearate and alkyl glucosides are commercially available under the Eumulgin® VL 75 brand.
  • alkyl and alkenyl oligoglycosides are therefore also used as third component (c).
  • R 1 is an alkyl and / or alkenyl radical having 4 to 22 carbon atoms
  • G is a sugar radical having 5 or 6 carbon atoms
  • p is a number from 1 to 10.
  • the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
  • the index number p in the general formula (I) indicates the degree of oligomerization (DP), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10.
  • the value p for a certain alkyl oligoglycoside is an analytically determined arithmetic parameter, which usually represents a fractional number.
  • Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferably used. From an application point of view, those alkyl and / or alkenyl oligoglycosides are preferred whose degree of oligomerization is less than 1.7 and is in particular between 1.2 and 1.4.
  • the alkyl or alkenyl radical R 1 can differ from primary alcohols with 4 to 11 preferably derive 8 to 10 carbon atoms. Typical examples are butanol, capro alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms.
  • Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and the technical mixtures described above, which can be obtained as well as their technical mixtures.
  • Alkylioligoglucosides based on hydrogenated C 1/2 coconut alcohol with a DP of 1 to 3 are preferred.
  • the amount of alkyl and / or alkenyl oligoglycosides used is usually 0.1 to 10 and preferably 1 to 5% by weight, based on the preparations .
  • Components (a) and (c) can be used in a weight ratio of 90:10 to 10:90, preferably 75:25 to 25:75 and in particular 60:40 to 40:60.
  • the emulsifiers depending on whether they are to be used for the production of W / O or O ⁇ V emulsions,
  • the amount of emulsifiers used which in turn may have a non-aqueous content of 30 to 100 and preferably 50 to 70% by weight, can be 1 to 20, preferably 2 to 10 and in particular 5 to 8% by weight, based on the final formulations. be.
  • the emulsifiers can be produced using the emulsifiers according to the invention, such as, for example, hair shampoos, hair lotions, foam baths, creams, lotions or ointments.
  • the formulations can contain mild surfactants, oil bodies, co-emulsifiers, superfatting agents, pearlescent waxes, consistency agents, thickeners, polymers, silicone compounds, biogenic active ingredients, antiperspirants, film formers, preservatives, Contain hydrotropes, solubi sators, UV light protection factors, antioxidants, insect repellents, self-tanners, perfumes, dyes and the like
  • Suitable mild, i.e. particularly skin-compatible surfactants are Fettaikoholpoly- ether sulfates, Monoglyce ⁇ dsulfate, mono- and / or dialkyl sulfosuccinates, FettsauNAthionate, Fettsauresarcosinate, Fettsauretaunde, fatty acid glutamates, Ethercarbonsauren, Alkyioligoglucoside Fettsaureglucamide, alkylamidobetaines and / or protein fatty acid condensates, the latter preferably based on wheat proteins
  • Guerbet alcohols based on fatty alcohols with 6 to 18, preferably 8 to 10 carbon atoms esters of linear C6-C22 fatty acids with linear C6-C22 fatty alcohols, esters of branched C6-Ci3 carboxylic acids with linear C6-C22- Fatty alcohols, esters of linear C6-C22 fatty acids with branched alcohols, especially 2-ethylhexanol, esters of hydroxycarboxylic acids with linear or branched C6-C22 fatty alcohols, especially dioctyl malates, esters of linear and / or branched fatty acids with polyhydric alcohols (e.g.
  • B propylene glycol, dimer diol or trimertylene) and / or Guerbet alcohols, triglycene based on C6-C10 fatty acids, liquid mono- / di- / tri-glycide mixtures based on C ⁇ -cis fatty acids, esters of C ⁇ -C22 fatty alcohols and / or Guerbet alcohols aromatic carboxylic acids, especially benzoic acid, esters of C2-Ci2-D ⁇ carbonsauren with linear or branched alcohols with 1 to 22 carbon atoms or polyo len with 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C ⁇ -C22 fatty alcohol carbonates, Guerbet carbonates, esters of benzoic acid with linear and / or branched C6-C22 alcohols ( eg Fmsolv® TN), linear or branched, symmetrical or asymmetrical
  • Suitable co-emulsifiers are, for example, nonionic surfactants from at least one of the following groups
  • adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycene mono- and diesters as well as sorbitan mono- and diesters of fatty acids or with ricinusol are known, commercially available products. These are homolog mixtures whose average degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out.
  • Ci2 / i8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 2024051 as refatting agents for cosmetic preparations
  • zwitterionic surfactants can be used as emulsifiers.
  • Zwitterionic surfactants are surface-active compounds which carry at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylammopropyl-N, N-dimethylammonium glycateate, for example cocoacylaminopropyldimethylammonium alkylglycinate, and 2-carboxylate -3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and coconut acylaminoethylhydroxyethylcarboxymethylglycate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylammopropyl-N, N-dimethylammonium glycateate, for example cocoacylamin
  • fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine is particularly preferred.
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C ⁇ / i ⁇ -alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SO3H group in the molecule and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkylimmodipropionic acids, N-hydroxyethyl-N-alkyiamidopropylglycine, N-alkyltauhne, N-alkylsarcosme, 2-alkylaminopropionic acids and alkylaminoacetic acids each with approximately aminoacetic acids 8 to 18 carbon atoms in the alkyl group.
  • ampholytic surfactants are N-coconut alkyl aminopropionate, the Cocosacylaminoethylaminopropionate and the Ci2 / i8-Acylsarcos ⁇ n
  • quaternary emulsifiers are also suitable, those of the ester quat type, preferably methyl-quaternized difatty acid urethane amine ester salts, being particularly preferred
  • Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithindene vates, polyol fatty acid esters, monoglycends and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers
  • Pearlescent waxes that come into question are, for example, alkylene glycol esters, especially ethylene glycol distearate, fatty acid alkanolamides, especially coconut fatty acid diethanolamide, partial glycides, especially stearic acid monoglycendants, esters of polyvalent, optionally hydroxy-substituted carboxylic acids with fatty alcohols with, for example, 6 to 22 carbon atoms, especially long, fatty acids, such as long Fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which have a total of at least 24 carbon atoms, especially lauron and distearyl ether, fatty acids such as stearic acid, hydroxystearic acid or behenic acid, ring opening products of olefin epoxides with 12 to 22 carbon atoms with fatty alcohols with 12 to 22 carbon atoms and / or polyols with 2 to 15 carbon atoms and 2 to 10
  • Possible consistency agents are primarily fatty alcohols or hydroxyfatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and also partial glycene ends, fatty acids or hydroxy fatty acids.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also high molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyacrylates, e.g.
  • Suitable cationic polymers are, for example, canonical cellulose derivatives, such as, for example, a quaternized hydroxyethyl cellulose, which is available under the name Polymer JR 400® from Amerchol, cationic starches, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers, such as, for example, luviquat ® (BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides, such as lauryldimomum hydroxypropyl hydrolyzed collagen (Lamequat®L / Grunau), quaternized wheat polypeptides, polyethyleneimine, canonical silicone polymers, such as amidomethicones, copolymers of adipic acid and dim - aminohydroxypropyldiethylenetamin (Cartaret ⁇ ne® / Sandoz), copolymers of acrylic acid
  • Anionic, zwitterionic, amphoteric and nonionic polymers include, for example, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobomylacrylate copolymers, methyl vinyl ether / maleic acid anhydride, and polyethylenethanol amide amide, and polyethylenethanol amide methacrylate and polyethylenethanol amide methacrylate and polyethylenethanol amide methacrylate and polyphenylene aminopolymers and their unsulfurized, n-amyl methacrylate aminopolymers and their polyunsulfonate acrylates and non-phenol aminophenyl acrylates and polyethylenes -Copolymers octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified silicone compounds, which can be both liquid and resinous at room temperature.
  • Fats are glycine, waxes include beeswax, carnauba wax, candelilla wax, montan wax, paraffin wax or microwaxes, if appropriate in combination with hydrophilic waxes, for example cetylstearyl alcohol or partial glycendones
  • hydrophilic waxes for example cetylstearyl alcohol or partial glycendones
  • Climbazole, octopirox and Zmkpyrethion can be used as antidandruff agents are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds.
  • Montmo can be used as a swelling agent and alkyl-modified carbopoitypene (Goodrich) are used.
  • Further suitable polymers or swelling agents can be found in the overview by R Lochhead in Cosm.Toil. 108, 95 (1993)
  • UV light protection factors are to be understood, for example, as organic or liquid substances (light protection filters) which are liquid or crystalline at room temperature and are able to absorb ultraviolet rays and the absorbed energy in the form of long-wave radiation, for example heat to deliver again.
  • UVB filters can be oil-soluble or water-soluble. Examples of oil-soluble substances are:
  • 3-benzylidene camphor or 3-benzyiide norcampher and its derivatives e.g. 3- (4-methylbenzylidene) camphor as described in EP-B1 0693471;
  • 4-aminobenzoic acid derivatives preferably 2-ethylhexyl 4- (dimethylamino) benzoate, 2-octyiester 4- (dimethylamino) benzoate and amyl 4- (dimethylamino) benzoate;
  • esters of cinnamic acid preferably 4-methoxycinnamic acid 2-ethylhexyl ester, 4-methoxycinnamic acid propyl ester, 4-methoxycinnamic acid isoamyl ester 2-cyano-3,3-phenylcinnamic acid 2-ethylhexyl ester (octocrylene);
  • esters of salicylic acid preferably 2-ethylhexyl salicylate, 4-isopropylbenzyl salicylate, homomethyl salicylic acid;
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
  • esters of benzalmalonic acid preferably di-2-ethylhexyl 4-methoxybenzmalonate
  • Triazine derivatives e.g. 2,4,6-trianilino- (p-carbo-2'-ethyl-1'-hexyloxy) -1, 3,5-triazine and octyl triazone, as described in EP-A1 0818450;
  • Propane-1,3-dione e.g. 1- (4-tert-butylphenyl) -3- (4'methoxyphenyl) propane-1,3-dione;
  • Sulfonic acid derivatives of 3-benzylidene camphor e.g. 4- (2-oxo-3-bomylidene-methyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bomylidene) sulfonic acid and their salts.
  • benzoylmethane such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione, 4-tert-butyl
  • benzoylmethane such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione, 4-tert-butyl
  • typical UV-A filters -4'-methoxydibenzoyl-methane (Parsol 1789), or 1-phenyl-3- (4'-isopropylphenyl) propane-1,3-dione.
  • the UV-A and UV-B filters can of course also be used in mixtures.
  • insoluble light-protection pigments namely finely dispersed metal oxides or salts, such as, for example, titanium dioxide, zinc oxide, iron oxide, aluminum oxide, cerium oxide, zirconium oxide, silicates (talc), barium sulfate and zinc stearate are also suitable for this purpose.
  • the particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm. They can have a spherical shape, but they can particles are also used which have an ellipsoidal shape or a shape which differs from the spherical shape in some other way.
  • Further suitable UV light protection filters can be found in the overview by P.Finkel in S ⁇ FW-Journal 122, 543 (1996).
  • secondary light stabilizers of the antioxidant type which interrupt the photochemical reaction chain, which is triggered when UV radiation penetrates the skin.
  • Typical examples are amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as D, L-camosine, D-camosine, L-carnosine and their derivatives (e.g. anserine) , Carotenoids, carotenes (e.g.
  • ⁇ -carotene, ⁇ -carotene, lycopene and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives (e.g. dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (e.g.
  • thioredoxin glutathione, cysteine, Cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -lineyl, cholesteryl and glyceryl esters) and their salts , Dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (eg buthioninsulfoximines, homocysteine sulfoximine, butioninsulfones, penta-, hexa-, himinathion) n very low tolerable doses (e.g.
  • ⁇ -hydroxy fatty acids e.g. citric acid, lactic acid, malic acid
  • humic acid e.g. citric acid, lactic acid, malic acid
  • bile acid bile extracts
  • bilirubin biliverdin
  • EDTA EDTA
  • EGTA unsaturated fatty acids and their derivatives
  • unsaturated fatty acids and their derivatives e.g. ⁇ -linolenic acid, linoleic acid, oleic acid
  • folic acid and their derivatives e.g. ⁇ -linolenic acid, linoleic acid, oleic acid
  • Ubiquinone and ubiquinol and their derivatives e.g. ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (e.g.
  • vitamin E acetate
  • vitamin A and derivatives vitamin A palmitate
  • coniferyl benzoate of the benzoin resin Rutinic acid and its derivatives, ⁇ -glycosylrutin, ferulic acid, furfurylidene glucitol, camosin, butylhydroxytoluene, butylhydroxyanisole, nordihydroguajakharzäure, nordihydroguajaretic acid, trihydroxybutyrophenon, uric acid and its derivatives, z
  • Selenium and its derivatives eg selenium methionine
  • stilbenes and their derivatives eg stilbene oxide, trans-stilbene oxide
  • derivatives salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids
  • Hydrotropes such as ethanol, isopropyl alcohol or polyols can also be used to improve the flow behavior.
  • Polyols that come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. Typical examples are • glycerin;
  • Alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;
  • Methyl compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
  • Lower alkyl glucosides in particular those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;
  • Sugar alcohols with 5 to 12 carbon atoms such as sorbitol or mannitol,
  • Aminosugars such as glucamine.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the other classes of substances listed in Appendix 6, Parts A and B of the Cosmetics Ordinance.
  • N, N-diethyl-m-touluamide, 1, 2-pentanedioi or Insect repellent 3535 are suitable as insect repellents, and dihydroxyacetone is suitable as a self-tanner.
  • Perfume oils include mixtures of natural and synthetic fragrances. Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, angelica, celery, cardamom, costus, iris, calmus), wood (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), Needles and twigs (spruce, fir, pine, mountain pine), resins and balms (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
  • Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethyl methyl phenyl glycinate, allyl cyclohexyl propylate pylate allylpropionate,
  • the ethers include, for example, benzyl ethyl ether, the aldehydes, for example, the linear alkanals with 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehy
  • fragrance oils which are mostly used as aroma components, are suitable as perfume oils, e.g. sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavandin oil.
  • perfume oils e.g. sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavandin oil.
  • the dyes which can be used are those substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40% by weight, based on the composition.
  • the agents can be produced by customary cold or hot processes; the phase inversion temperature method is preferably used.

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des émulsifiants contenant (a) des polyolpoly-12-hydroxystéarates et (b) des savons métalliques d'acides hydrocarboxyliques.
PCT/EP1999/003740 1998-06-08 1999-05-29 Emulsifiants WO1999064142A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2000553200A JP2002517306A (ja) 1998-06-08 1999-05-29 乳化剤
DE59907734T DE59907734D1 (de) 1998-06-08 1999-05-29 Emulgatoren
EP99939776A EP1093397B1 (fr) 1998-06-08 1999-05-29 Emulsifiants

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19825462A DE19825462C2 (de) 1998-06-08 1998-06-08 Emulgatoren
DE19825462.8 1998-06-08

Publications (1)

Publication Number Publication Date
WO1999064142A1 true WO1999064142A1 (fr) 1999-12-16

Family

ID=7870226

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/003740 WO1999064142A1 (fr) 1998-06-08 1999-05-29 Emulsifiants

Country Status (4)

Country Link
EP (1) EP1093397B1 (fr)
JP (1) JP2002517306A (fr)
DE (2) DE19825462C2 (fr)
WO (1) WO1999064142A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004514688A (ja) * 2000-11-29 2004-05-20 コグニス・ドイッチュランド・ゲゼルシヤフト・ミト・ベシュレンクテル・ハフツング・ウント・コンパニー・コマンデイトゲゼルシヤフト 化粧品用および／または薬剤用エマルジョン

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6905697B2 (en) 2001-01-19 2005-06-14 Sca Hygiene Products Gmbh Lotioned fibrous web having a short water absorption time
US6860967B2 (en) 2001-01-19 2005-03-01 Sca Hygiene Products Gmbh Tissue paper penetrated with softening lotion
DE10142124A1 (de) 2001-08-30 2003-03-27 Henkel Kgaa Umhüllte Wirkstoffzubereitung für den Einsatz in teilchenförmigen Wasch- und Reinigungsmitteln
EP2591046B1 (fr) 2010-07-09 2016-04-13 Alfa Klebstoffe AG Colle dotée d'un système tampon

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19533539A1 (de) * 1995-09-11 1997-03-13 Henkel Kgaa O/W-Emulgatoren
US5670478A (en) * 1992-09-07 1997-09-23 Galena, A.S. Pharmaceutical containing N-methylated cyclic undecapeptides
EP0868902A2 (fr) * 1997-04-01 1998-10-07 Henkel Kommanditgesellschaft auf Aktien Composition de teinture pour cheveux

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4420516C2 (de) * 1994-06-13 1998-10-22 Henkel Kgaa Polyglycerinpolyhydroxystearate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5670478A (en) * 1992-09-07 1997-09-23 Galena, A.S. Pharmaceutical containing N-methylated cyclic undecapeptides
DE19533539A1 (de) * 1995-09-11 1997-03-13 Henkel Kgaa O/W-Emulgatoren
EP0868902A2 (fr) * 1997-04-01 1998-10-07 Henkel Kommanditgesellschaft auf Aktien Composition de teinture pour cheveux

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004514688A (ja) * 2000-11-29 2004-05-20 コグニス・ドイッチュランド・ゲゼルシヤフト・ミト・ベシュレンクテル・ハフツング・ウント・コンパニー・コマンデイトゲゼルシヤフト 化粧品用および／または薬剤用エマルジョン

Also Published As

Publication number Publication date
DE19825462A1 (de) 1999-12-09
EP1093397B1 (fr) 2003-11-12
DE19825462C2 (de) 2001-03-08
DE59907734D1 (de) 2003-12-18
EP1093397A1 (fr) 2001-04-25
JP2002517306A (ja) 2002-06-18

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